I’m a junior day student at Lville. Here’s what I DM’d to OP (for anyone else looking for information on the school):
How are the dorms at each school (and are they spacious)?
Freshmen dorms: There are two dorms that freshmen live in, Dawes and Raymond, which are located directly across from each other on a “freshman-designated” lawn known as The Bowl. They were both renovated fairly recently (Summer 2019 and Winter 2020), so they’re actually quite nice and clean, though you will obviously be living with people who haven’t experienced boarding life before. Rooms tend to be kinda small, though it also depends on where exactly in the building you are—one good thing, however, is that almost everyone has a single.
Sophomore/junior dorms (Circle/Crescent Houses!)
There are six Circle Houses and five Crescent Houses, for boys and girls respectively. Each House has about 40 students—these are the years that you’ll be living in the famed Houses that Lawrenceville is known for. The buildings vary, and a lot of your experience depends on who the HoH (Head of House) is—my House, for example, is quite clean and has no odor; some Houses with more athletic-leaning populations or less strict HoHs may be messier (I spend significant amounts of time in another House where you might often see people’s stuff just randomly lying around).
The Circle Houses were built in the 1880s, with the exception of Hamill, which was built in 1814; the Crescent Houses were built in the 1980s, with the exception of Carter, which was built in 2010. Hamill and Carter are the nicest inside, and both have absolutely enormous common rooms.
The other four Crescent Houses are completely identical in construction, so your experience really depends on who your HoH is—Kirby, in particular is known for being the most strict. Note that all sophomore girls live in doubles, while junior girls have a mix.
The other five Circle Houses vary a lot. Cleve and Kennedy, for instance, are known for having triples (three bedrooms attached by a common room); Woodhull, on the other hand, has only five doubles (three for sophomores, two for juniors)—everyone else lives in a single. The rooms are generally quite spacious, though the larger ones tend to be reserved for juniors and prefects. I will say that in my House, there are three rooms on the second floor that always go to sophomores known as “the closets,” which are absolutely tiny; there’s also a triple in Kennedy where the individual rooms are so small that the bed is bunked with the desk underneath it. I don’t know a single junior with a small room though. In my experience, Circle Houses also have far cleaner bathrooms than Lower (Raymond/Dawes), though I experienced pre-renovation Raymond, and apparently post-renovation Raymond is far nicer.
One thing to note about the House system is that it really builds community. Your closest friends tend to be in your House (though you aren’t restricted by any means—I chill in other Houses all the time). Your Head of House is often one of your main confidants on campus. You get your feeds at your House. You return to your House as a senior to reminisce about the “good ol’ days.” You wear House merchandise everywhere (I’m currently in India wearing a hoodie branded with my House’s logo). You yell your House’s chant around campus and defend it during House Olympics. Even day students have Houses as their home base. It’s wonderful.
Senior dorms:
Upper, where almost all senior boys live, is absolutely massive. They have a game room with four TVs, multiple pool and ping-pong tables, a piano—there’s something like 80 people living there. It’s also directly attached to (as in, it’s in literally the same building as) Abbott, the senior dining hall. They also have really cool rooms like quads, and they’re very very spacious. On the flip side, however, one of my senior friends described Upper as “more an apartment building than a House.”
You probably won’t end up in Kinnan; there’s about 10 senior boys who live there each year. There’s a very specific type of student who goes to Kinnan—you’ll understand more if you come here 
McPherson and Reynolds are the two girls’ senior Houses, and they’re basically two mini-Uppers in two buildings. McPherson is from the 1920s, while Reynolds is from the 1980s. I have never entered either, so I cannot comment further.
How much time is allocated towards homework at each school, and is the workload manageable?
We have study hall from 8:00 PM to 10:00 PM every weekday, where the entire House has to be quiet. For freshmen, it’s even more stringent; you have to put your phone outside your room, you have to ask to get out of your chair, etc—for sophomores and above, it’s a lot more free; you can even go to the Library! (don’t go to the Library; no one gets work done there). I personally use my free periods, lunch periods, and consultation to also get some work done; usually, my goal is to have at least half of the following day’s homework finished by the end of the school day. As a freshman/sophomore, it’s a bit easier, though—I was often able to do my homework during the lunch breaks before class, but that’s not sustainable now (I’m a junior).
The workload is what you make of it. I know a lot of people who overextend themselves—I personally don’t, and I’m completely fine. There is a general “grind culture” here (I’m sure it’s similar at Andover; did you see that video posted in Miscellaneous Ramblings?) which tempts people to do way more than they should; don’t fall into that trap.
What kinds of resources are there at each school that aim towards accommodating incoming freshman and helping them to adjust to the boarding school environment?
I’m a day student, so I can’t help with the latter part, but here’s a few things:
- During freshman fall, three of your five classes (everything but math and language, because those classes often have non-freshmen in them) are pass-fail, allowing you to focus on socialization.
- You get a free period during freshman fall to help learn time management.
- As I described earlier, freshmen have a far stricter study hall.
- “Grade bonding” is really emphasized during freshman year. Throughout the year (and especially during orientation week), you have a lot of freshman-only events where you can mix with people in your own grade—a bit of “mandatory fun,” in other words :).
- The freshmen also have a more insular experience; you stay around The Bowl rather than around The Circle (and The Bowl is the primary outdoor socialization spot for freshmen; it’s a bit of an unspoken rule that upperclassmen don’t really go there), and your dining hall is also on a different floor from the sophomores and juniors.
How many opportunities are there for students to visit family back home that aren’t during major breaks?
We have quite a few long weekends. This past Winter Term (10 weeks), we had exactly two weeks where we had no days off. There’s also some long weekends (~4 days) like Parent’s Weekend and Winter Gathering that happen once per term.
Can family come visit you anytime they’d like?
Yes.
How many opportunities are there for students to leave campus or are students allowed to do so anytime they’d like whenever they do not have classes?
Freshmen, sophomores, and juniors can leave after classes on Wednesdays and Saturdays, as well as any time on Sundays, as long as they’re back by 7:00 PM (later returns aren’t allowed unless it’s a sleepover, which tends to have its own complications). You do need to get your HoH to sign off on it, though.
Seniors can leave at any time when they don’t have a required commitment like classes or sports. There is no specific permission required. Again, they must be back by 7:00 PM.